Between the October 1908 and the June 1909 UMC price lists UMC dropped the unique head-stamps for their NPEs and began stamping "HAND LOADED" on the paper tube. From the 1910 Catalogue --
1910 NEW CLUB NPEs.jpeg
In 1911, Marcellus Hartley Dodge combined his arms and ammunition companies as Remington Arms - Union Metallic Cartridge Co. So, from 1911 on the head-stamp became Remington-UMC --
1911-12 NEW CLUB NPEs.jpeg
By the 1915-16 Remington Arms - Union Metallic Cartridge Co. catalogue the head-stamp had become REM-UMC --
1915-16 Catalog NEW CLUB NPEs.jpeg
E.K. Tryon either hadn't updated their pictures or they were attempting to move some old stock. Also, of note, circa 1901 UMC went to the eight-pointed star around the primer pocket on both their NEW CLUB and UNION black powder hulls, another clue for the shells in question being from the 1890s.